This invention relates to herbicidally active sulfonamide compounds, agriculturally suitable compositions thereof and a method of their use as general and/or selective herbicides or plant growth regulants. More specifically, this invention relates to herbicidally active sulfonamides having an ortho-acyl group or a derivative thereof ortho to the sulfonyl bridge.
In the most common situation, the control of undesired vegetation is desired to permit the growth of useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such useful crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
U.S. Pat. Nos. 4,169,719 and 4,127,405 disclose herbicidal benzenesulfonamides having a substituent ortho to the sulfonyl group.
U.S. Pat. No. 4,370,480 discloses herbicidal benzenesulfonamides of formula ##STR1## wherein R is ##STR2## T is O; and R is alkyl or substituted alkyl.
U.S. Pat No. 4,481,029 discloses, in part, thiophenesulfonamides of formula ##STR3## wherein A is ##STR4## R.sup.II is alkyl, alkenyl, phenyl, benzyl or substituted phenyl or benzyl; and
B is ##STR5## PA1 R is H, C.sub.1 -C.sub.12 alkyl, etc.; PA1 R.sub.6 is H, C.sub.1 -C.sub.6 alkyl, allyl, etc.; or PA1 R and R.sub.6 can be taken together to form ##STR8## PA1 R.sub.4 is H or alkyl; PA1 A is Y(CH.sub.2).sub.n R.sub.17 or ##STR11## Y is O, S or a single bond; n is 0 or 1; and PA1 R.sub.17 is a 5- or 6-membered saturated heterocycle. PA1 C is CO, CR.sub.21 R.sub.22 or SO.sub.2. PA1 J is ##STR15## Q is a saturated 5- or 6-membered ring containing 1 or 2 heteroatoms selected from 0-1 oxygen, 0-1 sulfur and 0-1 nitrogen, or Q is an unsaturated or partially unsaturated 5- or 6-membered ring containing 1-3 heteroatoms selected from 0-1 sulfur, 0-1 oxygen and 0-3 nitrogen; or Q is a saturated 3- or 4-membered heterocyclic ring containing one nitrogen atom and is bonded to G through said nitrogen; and Q may be optionally substituted by 1-4 groups selected from L; PA1 G is a C.sub.1 -C.sub.3 alkyl radical in which one of the carbons must be substituted with R.sub.2 and/or R.sub.3, and the remaining carbon atoms may optionally be substituted with 1 or 2 substituents selected from CH.sub.3, F and Cl; PA1 R is H or CH.sub.3 ; PA1 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CO.sub.2 R.sup.III, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 CN, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 R.sub.2 is OH, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 R.sub.3 is OCH.sub.3 or OC.sub.2 H.sub.5 ; or PA1 R.sub.2 and R.sub.3 can be taken together to form a carbonyl group, or the 5- or 6-membered ring ketal or thioketal thereof; PA1 R.sup.I is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalyl, methoxy or ethoxy; PA1 R.sup.II is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sup.I and R.sup.II may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sup.III is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 L is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkenylthio, C.sub.1 -C.sub.2 haloalkoxy or C.sub.1 -C.sub.2 haloalkylthio; PA1 A is ##STR16## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C(O)R.sub.4, ##STR17## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.5 and R.sub.6 are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.4 is H or CH.sub.3 ; PA1 Z is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 Y.sub.2 is H or CH.sub.3 ; PA1 X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA1 Y.sub.3 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OCH.sub.2 CH.sub.3, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (b) when X or Y is OCF.sub.2 H, then Z is CH; PA1 (c) when J is J-2 or J-3, then GQ and the sulfonylurea bridge must be on adjacent carbon atoms; PA1 (d) when Q is bonded to G through nitrogen, then the adjacent carbon atom of G cannot be substituted with OH, F or Cl; PA1 (e) when G is C.sub.1 alkyl in the form of a carbonyl group, then Q is other than ##STR18## (f) when the total number of carbon atoms of X and Y is greater than four, then the total number of carbon atoms of R.sub.1 and GQ must be less than or equal to ten; PA1 (g) when W is S, then A is A-1, R is H, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3 or CH(OCH.sub.3).sub.2 ; and PA1 (h) when R.sub.3 is OCH.sub.3 or OC.sub.2 H.sub.5, then R.sub.2 is other than OH. PA1 W is O; and PA1 R is H; PA1 R.sub.11 and R.sub.12 are independently H, CH.sub.3 or OCH.sub.3 ; and PA1 R.sub.13 and R.sub.14 are independently CH.sub.3 or OCH.sub.3 ; PA1 G is a carbonyl group, or is a single carbon atom substituted with OH, OCH.sub.3 or OC.sub.2 H.sub.5 ; and PA1 R.sub.1 is H, CH.sub.3, OCH.sub.3, SCH.sub.3, SO.sub.2 CH.sub.3, F, Cl, Br, NO.sub.2, CH.sub.2 CN, CF.sub.3 or OCF.sub.2 H; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH=CH.sub.2, OCH.sub.2 C.tbd.CH, CH.sub.2 OCH.sub.2 CH.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, SCF.sub.2 H, C(O)R.sub.4, ##STR20## OCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3 ; PA1 A is A-1; PA1 R.sub.1 is H, CH.sub.3, OCH.sub.3, SCH.sub.3 or Cl; and PA1 G is a carbonyl group or a single carbon atom substituted with OH; PA1 X is CH.sub.3, OCH.sub.3, Cl or OCF.sub.2 H; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, CH(CH.sub.3).sub.2, NHCH.sub.3, CH(OCH.sub.3).sub.2 or cyclopropyl; PA1 J is J-1; and PA1 R.sub.1 is in the 5-position; PA1 J is J-2; and PA1 R.sub.1 is H; PA1 J is J-3; and PA1 R.sub.1 is H; PA1 J is J-4; and PA1 R.sub.1 is H; PA1 J is J-5; and PA1 R.sub.1 is H; PA1 J is J-6; and PA1 R.sub.1 is H; PA1 Q is a saturated 5- or 6-membered ring which is bonded through a carbon atom and contains 1 heteroatom selected from oxygen or sulfur, or an unsaturated or partially unsaturated 5- or 6-membered ring which is bonded through a carbon atom and contains 1-3 heteroatoms selected from 0-1 sulfur, 0-1 oxygen or 0-3 nitrogen; and Q may be optionally substituted by 1-4 groups selected from L; PA1 G is a carbonyl group or CHR.sub.2 ; PA1 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II. C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl or CO.sub.2 R.sup.III ; and PA1 A is A-1, A-2, A-3, A-4, A-5 or A-6. PA1 Q is Q.sub.1 -Q.sub.21, Q.sub.24 -Q.sub.32 and Q.sub.34 -Q.sub.38 ; PA1 M is Cl, Br or NO.sub.2. PA1 M is Cl, SO.sub.2 NH-t-butyl; or SO.sub.2 NHSi(CH.sub.3).sub.2 C(CH.sub.3).sub.3 ; PA1 M is Cl, Br or SO.sub.NH-t-butyl; and PA1 Z is CH or N. PA1 R.sub.1 is H, Cl, Br, C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.3 thioalkyl or NO.sub.2 ; PA1 M is Cl, Br or C.sub.2 -C.sub.4 alkyl- or benzylthio; PA1 Z=CH or N; and PA1 J=H or Cl.
U.S. Pat. No. 4,491,467 discloses, in part, herbicidal benzenesulfonamides of formula ##STR6## wherein A is a 5- or 6-membered aromatic heterocycle, a 5-or 5-membered dihydroaromatic heterocycle or a 6-membered tetrahydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms, and/or 0-4 nitrogen atoms; the heterocycles may be optionally substituted with 1-4CH.sub.3, 1-2OCH.sub.3, 0-1 SCH.sub.3, 0-1 Cl, 0-1 N(CH.sub.3).sub.2 or 0-1 CN groups.
U.S. Pat. No. 4,394,506 discloses, in part, herbicidal sulfonylureas of the formula ##STR7## wherein Q is O, S or NR.sub.6 ;
South African Patent Application No. 83/8416 (published 5/12/84; Swiss priority 11/12/82) discloses herbicidal sulfonylureas of formula ##STR9## wherein, in part, A is an unsaturated or only partially saturated 5- or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms and which may be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.8 alkoxyalkyl, di(C.sub.1 -C.sub.4 alkyl)amino, halogen, cyano or nitro.
EP-A-141,777 (published 5/15/85; Swiss priority 9/9/83) discloses herbicidal sulfonylureas of the formula ##STR10## wherein R.sub.3 is H, alkyl, haloalkyl or CN;
EP-A-116,518 (published 8/22/84; Swiss priority 2/4/83) discloses herbicidal sulfonylureas of the formula ##STR12## wherein X is NR.sub.6 R.sub.7, N(SO.sub.2 R.sub.9).sub.2 or ##STR13## A is CO, SO.sub.2, CONR.sub.23 or CO.sub.2 ; B is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkylene; and